Substantive orthooxyazo dyestuffs and process of making same.



warren snares Parana orraon.

EUGEN ANDERWERT, HERMANN FRITZSCHE, AND HEINRICH SCHOBEL, 0F BASEL, SWITZERLAND, ASSIGNORS TO SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF

BASEL, SWITZERLAND.

SUBSTANTIVE ORTHOOXYAZO DYESTUFFS AND PROCESS 0E MAKING SAME.

No Drawing.

To all whom it may concern:

Be it known that we, EUGEN ANDERWERT, HERMANN FRITZsGHE, and HEINRICH Sono- BEL, all three chemists and citizens. of the Swiss Republic, and residents of Basel, Switzerland, have invented new Substantive Orthooxyazo Dyestuffs and Processes of Making Same, of which the following is a full, clear, and exact specification.

Orthoamidophenol and its derivatives have been employed hitherto exclusively for the manufacture of orthooxyazodyestuffs dyeing mordanted wool, and never for the manufacture of substantive dyestuffs dyeing unmordanted cotton. \Ve have now found that the azodyestuifs containing a diazoderivative of orthoan'lidophenol or of one of its derivatives on the one hand and a 2: 5: 7-aminonaphtholsulfonic compound corresponding to the formula SOELRA'AW NHX wherein X stands for CO-(l) c H Nmo) NH 2 -coommon 5 803B: (7)

pared by combining an orthooxydiazobody of the aromatic series only with a 2:5 :7- aminonaphtholsulfonic or 2 5 1 7-am1no- Specification of Letters Patent.

Application filed October 6, 1915.

Patented @ct. 22?, 1918.

Serial No. 54,403.

naphtholdisulfonic compound or by combining first 1 molecule of an orthooxydiazobodyof the aromatic series with '1 molecule of a 2:5:7-aminonaphtholsulfonic or 2:51:7-

aminonaphtholdisulfonic compound and afterward the resulting intermediate product with 1 molecule of an aromatic diazobody.

The invention is illustrated by the following examples:

Example 1: 15.4 kg. 4:2:1-nitroaminophenol are diazotized in the usual way and the resulting diazocompound is poured into.

a solution of 37 kg. metaaminobenzoyl- 2 5 7-aminonaphtholsulfonic acid and of 30 kg. sodium carbonate in water. After 2% hours the mass is heated to 40 C. and the dyestutf precipitated by addition of common salt and isolated as usual. It dissolves in water to a violet solution turningto red on addition of NaOH and dyes cotton dull roseate shades. Diazotized on the fiber and developed with betanaphthol the tintsbecome more yellowish.

1 Example 2: The diazoderivative of 15.4 kg. nitroaminophenol is poured into a solution of 52 kg,

and of 30 kg. sodium carbonate in water. After a short time the combination is achieved and the dyestufi is isolated in the usual manner. It dissolves in water to a violet solution, turning to brownish-red on addition of 'NaOH and dyes cotton dull blue-violet shades which become dull chestnut-brown, when developed on the fiber with paranitrodiazobenzene.

Example 3: 37 :8 kg. orthoamidophenolsulfonic acid are converted into the corresponding diazocompound and this latter is poured into a solution of 50. 1 k

W I to and of 50 kg. sodium carbonate in Water.

After 24c'hours thevdyestult' is separated as usual. It dissolves in water to a cherryred'solution becoming bluish-red on addition of NaOH and dyes cotton scarlet-red tints.

Example 4: To a solution of 50st kg. of the derivative of 2:527-aminonaphtholsultonic. acid employed in Example 3 and of 50 km of sodium carbonate in water is added the diazoderivative of 30.8 kg. 2: l-nitroaminophcnol and after 2% hours the dyestuff is isolated in the usual manner. It dissolves in water to a blue solution turning to bluish-red on addition of NaGH and dyes cotton roseate tints.

Instead of the diazophenol derivatives indicated in the examples, can be employed the corresponding diazoacidylphenol derivatives able to combine more easily, the resulting dyestuffs being saponified after their preparation.

The new dyestuffs are not only suitable- SOIE\ wherein X stands for OaH on a 1o !r( 2. The described process for the manufacture of'new. substantive orthooxydyeistufis consisting in combining. first 1 molecule of an orthooxydiazobody of the aromatic se ries with 1 molecule of a 2:5:7-aminonaphtholsulfonic compound corresponding to the formula t 1 A I i v soun anai.

wherein X stands for an 2 -coclunt on (5 son 7 Y on (s) -o 56 sonim and afterward the resulting intermediate product with 1 molecule of an aromatic diazobody.

As new products the described ortho oxyazodyestutfsderived from an ort'hooxydiazobody of the aromatic series and a :2 :7 aminonaphtholsuliioni 0 compound cor responding to the formula wherein X stands for NH 2 430- .c mon 5 son; 7

on (a) 1o s\ sonl 7 constituting intense colored powders, yielding with concentrated. sulfuric acid deep colored solutions, dissolving in'water to solutions changing their coloration intensively on addition of sodium carbonate or of soda lye and dyeing cotton, wool, silk, mixed goods, straw, wood and paper according to the methods used for the known substantive dyestuffs.

4. As new products the described orthooxyazodyestuffs derived from 1 molecule of an orthooxydiazobody of the aromatic series, 1 molecule of a further aromatic diazobody and 1. molecule of a 2 5 'Y-aminonaphtholsulfonic compound corresponding to the formula NHX wherein. X stands for NH (2)-CO- iuHbOH on a -c n w son1 1 constituting intense colored powders, yielding with concentrated sulfuric acid deep catered SOllt1-G1S,-dlSSQlVll'lg 111. water to solutions changing their colorntions inten- SiVGLY on addition of sodium carbonate or of soda lye and dyeing cotton, wool, silk, mixed goods straw, Wood and paper acoording to tho methods used for the known snhstantivo dyvstutfs. i

in witness whereof we have hereunto signed our names this 17th day of September 1915, in the presence of two subscribing Witnesses.

EUGEN ANDERWER-T. DR. HERMANN FRITZSGHE. D11. HEINRICH SCHOBEL. 'itnesses:

ARNOLD ZUBER, ARMANI) BITTER. 

